<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2603</id>
  <title>T3D2562</title>
  <common-name>Gamma-Butyrolactone</common-name>
  <description>One of the furans with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.</description>
  <cas>96-48-0</cas>
  <pubchem-id>7302</pubchem-id>
  <chemical-formula>C4H6O2</chemical-formula>
  <weight>86.036780</weight>
  <appearance>Colorless oily liquid (L1140).</appearance>
  <melting-point>-45°C</melting-point>
  <boiling-point></boiling-point>
  <density></density>
  <solubility>1000.0 mg/mL</solubility>
  <specific-gravity></specific-gravity>
  <flash-point></flash-point>
  <vapour-pressure></vapour-pressure>
  <route-of-exposure>Inhalation (A626) ; oral (A626) ; injection (A626) ; dermal  (A626).</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Gamma-butyrolactone is rapidly converted to gamma-hydroxybutyrate. This may account for the subsequent central nervous system depressant. Gamma-butyrolactone is an anesthetic that causes a selective increase in brain dopamine by antagonizing transmitter release from nerve terminal. It is also an endogenous brain metabolite that may be derived from glutamate through gamma-aminobutyrate. GBL binds to the picrotoxin receptor (A566, A318).</mechanism-of-toxicity>
  <metabolism>Gamma-Butyrolactone undergoes rapid and quantitative conversion by lactonases, yielding gamma-hydroxybutyric acid (A627). </metabolism>
  <toxicity>LD50: 17.2 mL/kg (Oral, Rat) (581)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>Common solvent and reagent in chemistry and is used as an aroma compound, as a stain remover, as a superglue remover, as a paint stripper, and as a solvent in some wet aluminium electrolytic capacitors (L1140).</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>CNS depression; amnesia and hypotonia. Rarely, hypertension, orthostatic hypotension, apnea, dyskinesias, dystonias, and hypomania occur.</health-effects>
  <symptoms>Headache, confusion, ataxia, urinary incontinence or urgency, difficulty breathing, bradycardia, uncontrollable shaking, hallucinations, seizure-like activity (uncontrollable or unusual movements), and acidosis. Hypothermia has been reported in adults and children following exposure (T36).
</symptoms>
  <treatment>In case of oral exposure, administer a benzodiazepine IV. There is no antidote. Treatment is symptomatic and supportive. (T36)
</treatment>
  <created-at type="dateTime">2009-07-05T03:12:29Z</created-at>
  <updated-at type="dateTime">2026-03-26T21:07:39Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/4-Hydroxybutyric acid lactone</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C01770</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>42639</chebi-id>
  <biocyc-id>CPD-10135</biocyc-id>
  <ctd-id>D015107</ctd-id>
  <stitch-id>Butyrolactone, gamma-</stitch-id>
  <drugbank-id>DB04699</drugbank-id>
  <pdb-id>GBL</pdb-id>
  <actor-id>227</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>O=C1CCCO1</moldb-smiles>
  <moldb-formula>C4H6O2</moldb-formula>
  <moldb-inchi>InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2</moldb-inchi>
  <moldb-inchikey>YEJRWHAVMIAJKC-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">86.0892</moldb-average-mass>
  <moldb-mono-mass type="decimal">86.036779436</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Liquid</state>
  <logp>-0.64</logp>
  <hmdb-id>HMDB00549</hmdb-id>
  <chembl-id>CHEMBL95681</chembl-id>
  <chemspider-id>7029</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Fabio Giannessi, Maria Ornella Tinti, Francesco De Angelis, &amp;#8220;Process for producing&amp;#174;-3-hydroxy-4-butyrolactone useful for preparing&amp;#174;-carnitine.&amp;#8221; U.S. Patent US6127552, issued February, 1998.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002088</chemdb-id>
  <dsstox-id>DTXSID6020224</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>oxolan-2-one</iupac>
</compound>
